Benzaldehyde → 1-isopropyl-4-phenyl-3,4,6,7-tetrahydro-furo[3,2-g] quinazolin-2(1H)-one

HRID 1658287Notes

Reaction equation

HRID 1658287 reaction equation
[CH:1]([N:4]([C:8]1[CH:16]=[CH:15][C:11]2[CH2:12][CH2:13][O:14][C:10]=2[CH:9]=1)[C:5]([NH2:7])=[O:6])([CH3:3])[CH3:2].[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CS(O)(=O)=O.C1(C)C=CC=CC=1>[CH:1]([N:4]1[C:8]2[C:16](=[CH:15][C:11]3[CH2:12][CH2:13][O:14][C:10]=3[CH:9]=2)[CH:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[NH:7][C:5]1=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 21528985N-(2,3-Dihydro-1-benzofuran-6-yl)-N-propan-2-ylurea

Product 1

HCID 215289561-isopropyl-4-phenyl-3,4,6,7-tetrahydro-furo[3,2-g] quinazolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 1140TolueneSolvent

Procedure

A solution of 8.0 g. of 1-Isopropyl-1-(2,3-dihydro-6-benzofuranyl)urea, 3.6 ml. of benzaldehyde, 5 drops of methanesulfonic acid and 200 ml. of toluene is stirred and refluxed under a water separator for 20 hours. The resulting solution is cooled and the cooled solution is washed twice with 150 ml. water, dried with anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue is dissolved in a minimum amount of chloroform and chromatographed on silica gel (200 g.) using chloroform as an eluent to give an oil of 1-isopropyl-4-phenyl-3,4,6,7-tetrahydro-furo[3,2-g] quinazolin-2(1H)-one and an oil of 6-isopropyl -9-phenyl-2,3,8,9-tetrahydro-furan[2,3-f]quinazolin-7(6H)-one.

Workup

  1. temperaturerefluxed under a water separator for 20 hours
  2. temperatureThe resulting solution is cooled
  3. washthe cooled solution is washed twice with 150 ml
  4. dry with materialwater, dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue is dissolved in a minimum amount of chloroform
  8. customchromatographed on silica gel (200 g.)

Sources & evidence

ORD record
ord-8f0bc856b5074eeabfd39323e8bef263
Source dataset
uspto-grants-1976_06
Patent number
US03963717

Reaction notes

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